JPH03100060A - Water-and oil-repellent wax additive - Google Patents
Water-and oil-repellent wax additiveInfo
- Publication number
- JPH03100060A JPH03100060A JP23698089A JP23698089A JPH03100060A JP H03100060 A JPH03100060 A JP H03100060A JP 23698089 A JP23698089 A JP 23698089A JP 23698089 A JP23698089 A JP 23698089A JP H03100060 A JPH03100060 A JP H03100060A
- Authority
- JP
- Japan
- Prior art keywords
- wax
- water
- silane compound
- fluorine
- containing silane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000654 additive Substances 0.000 title claims abstract description 11
- 230000000996 additive effect Effects 0.000 title claims abstract description 9
- 239000005871 repellent Substances 0.000 title description 2
- -1 fluorinated silane compound Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 229910000077 silane Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 239000002904 solvent Substances 0.000 abstract description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 abstract 1
- 239000001993 wax Substances 0.000 description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003373 anti-fouling effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001365789 Oenanthe crocata Species 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、撥水、撥油性ワックス添加剤に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to water- and oil-repellent wax additives.
従来のワックスは、天然ワックス、合成ワックス、配合
ワックスなどがあり、此れ等は繊維、紙等に含浸させて
耐水性を増加させたり、金属表面にコーティングするこ
とによって耐水性、防汚性を高めるカーワックスや、金
型において樹脂との離型性を高める離型剤等に使用され
ている。Conventional waxes include natural waxes, synthetic waxes, and blended waxes. These waxes can be impregnated into fibers, paper, etc. to increase water resistance, or coated on metal surfaces to improve water resistance and stain resistance. It is used in car waxes that increase the temperature of the product, and mold release agents that improve the release properties from resin in molds.
しかし、従来のワックスはパラフィン系の炭化水素であ
るため、繊維、紙等に含浸させて耐水性を増加させる用
途に用いた場合、耐水性、防汚性が充分でなく、また有
機溶剤によってワックス自体が溶解して除去される問題
があった。However, since conventional wax is a paraffin-based hydrocarbon, when used to increase water resistance by impregnating fibers, paper, etc., it does not have sufficient water resistance or stain resistance, and wax There was a problem that the material itself would dissolve and be removed.
これらの問題を解決するために、フッ素系の化合物を添
加剤として用いる方法も検討されているが、前記問題は
未だ充分に解決されていない。In order to solve these problems, methods of using fluorine-based compounds as additives have been studied, but the problems have not yet been satisfactorily solved.
本発明者等は、上記課題を検討した結果、分子中にペル
フルオロアルキル基とシリル基を有する特定の含フツ素
シラン化合物が前記課題を解決することを見出した。As a result of studying the above problems, the present inventors found that a specific fluorine-containing silane compound having a perfluoroalkyl group and a silyl group in the molecule solves the above problems.
本発明は、一般式
％式％（１）
（式中Ｒ，は炭素数４〜１２のペルフルオロアルキル基
、ｎは０〜３の整数、ｍ、ｆｌは１〜３の整数。The present invention is based on the general formula % (1) (wherein R is a perfluoroalkyl group having 4 to 12 carbon atoms, n is an integer of 0 to 3, and m and fl are integers of 1 to 3.
ＹはＣＨ，、ＣＨ，０、ＮＲ１、ＣＯ□、Ｃ０ＮＲ’、
Ｓ、ＳＯ，，５０２ＮＲ”、Ｒ”は水素、または炭炭素
数４〜５のアルキル基、Ｒ２は炭炭素数４〜５のアルキ
ル基、ＸはＣ１、Ｂｒ、または炭炭素数４〜５のアルコ
キシ基）で表される含フツ素シラン化合物からなるワッ
クス添加剤を提供するものであり、特に該含フツ素シラ
ン化合物が一般式
％式％（）
（式中Ｒ２、Ｘは前記に同じ）で表わされるワックス添
加剤を提供する。Y is CH,, CH,0, NR1, CO□, C0NR',
S, SO,,502NR", R" is hydrogen or an alkyl group having 4 to 5 carbon atoms, R2 is an alkyl group having 4 to 5 carbon atoms, X is C1, Br, or an alkyl group having 4 to 5 carbon atoms The present invention provides a wax additive consisting of a fluorine-containing silane compound represented by an alkoxy group), and in particular, the fluorine-containing silane compound has the general formula % () (in which R2 and X are the same as above) A wax additive is provided.
本発明における含フツ素シラン化合物は、既に特願昭６
３−１０１４６号等として特許出願されているが、ワッ
クスへの適用は知られていない。The fluorine-containing silane compound in the present invention has already been disclosed in a patent application filed in 1983.
Although a patent application has been filed as No. 3-10146, its application to wax is not known.
本発明の一般式（１）で表される含フツ素シラン化合物
において、Ｒ，は炭素数４〜１２のペルフルオロアルキ
ル基であり、このペルフルオロアルキル基が、撥水、撥
油性、非粘着性、防汚性を付与し、ワックスの耐水性の
みならず耐有機溶剤性をも与える。この効果は、（ｎ）
式で表される化合物において一層顕著であり、これは該
化合物中のスルホンアミド結合が、ペルフルオロアルキ
ル基の外表面への配向を高めるためと考えられる。In the fluorine-containing silane compound represented by the general formula (1) of the present invention, R is a perfluoroalkyl group having 4 to 12 carbon atoms, and this perfluoroalkyl group has water repellency, oil repellency, non-stick properties, Provides antifouling properties and provides not only water resistance of wax but also organic solvent resistance. This effect is (n)
This is more noticeable in the compound represented by the formula, and this is thought to be because the sulfonamide bond in the compound increases the orientation of the perfluoroalkyl group to the outer surface.
一方、シリル基の正確な効果は不明であるが。On the other hand, the exact effect of the silyl group is unclear.
類似の分子構造を持っていてもシリル基を有さない化合
物においては充分な特性が得られないことから推察する
と、シリル基はペルフルオロアルキル基の表面への配向
、または含フツ素シラン化合物のワックス中における表
面へのブリード等において何等かの作用を有していると
思われる。It can be inferred from the fact that sufficient properties cannot be obtained with compounds that do not have a silyl group even if they have a similar molecular structure. It seems that it has some effect in bleeding to the surface inside.
また、シリル基に結合しているアルキル基は、水分を含
んだワックス中ないし空気中における加水分解性を抑え
ると共に、ワックス、および溶媒への溶解性を高める。Furthermore, the alkyl group bonded to the silyl group suppresses hydrolysis in wax containing moisture or in the air, and increases solubility in wax and solvent.
本発明が適用されるワックスは特に限定されず、天然ワ
ックス、合成ワックス、配合ワックスなどを包含する。The waxes to which the present invention is applied are not particularly limited, and include natural waxes, synthetic waxes, blended waxes, and the like.
含フツ素シラン化合物の添加量はワックスの種類によっ
て変化するが、０．１〜１０重量％の間で変化できる。The amount of the fluorine-containing silane compound added varies depending on the type of wax, but can range from 0.1 to 10% by weight.
０．１重量％以下であると撥水、撥油性、非粘着性、防
汚性において効果がなく、１０重量％以上であるとそれ
以下の場合と比較して特性的に大きな変化はない。If it is less than 0.1% by weight, there will be no effect in terms of water repellency, oil repellency, non-adhesiveness, and antifouling properties, and if it is more than 10% by weight, there will be no significant change in properties compared to the case where it is less than that.
ワックスへの添加法は、（１）式または（ＩＩ）式で示
される含フツ素シラン化合物自身、またはそれを含む有
機溶媒溶液をワックスに添加することによって行われる
。溶媒としては、ハロゲン化炭化水素、アルコール、エ
ーテルなどが好ましく、無水または必要に応じてアミン
または酸の水溶液を少量添加したものが使用される。こ
こで用いるアミンは、−級アミン、二級アミン、三級ア
ミンのいずれでもよいが、特に−級アミンが有効である
。The addition method to the wax is carried out by adding the fluorine-containing silane compound represented by the formula (1) or (II) itself or an organic solvent solution containing the same to the wax. As the solvent, halogenated hydrocarbons, alcohols, ethers, etc. are preferred, and anhydrous ones or those to which a small amount of an aqueous solution of an amine or acid is added as necessary are used. The amine used here may be any of -class amines, secondary amines, and tertiary amines, but -class amines are particularly effective.
また、用いる酸としては、塩酸、硫酸、硝酸、燐酸など
の無機酸、蟻酸、酢酸、シュウ酸、トルエンスルホン酸
などの有機酸が利用できる。酸の水溶液を用いた場合に
は、水溶液中の水は含フツ素シラン化合物のハロゲノシ
リル基またはアルコキシシリル基を加水分解してヒドロ
キシシリル基を形成し、分子間の縮合を増加させるか、
またはワックス成分中に水酸基を有したものについては
、その成分と化学反応をする作用を持つ。また、酸及び
アミンは、この加水分解および脱水縮合を促進させる触
媒の役目を果たすものである。これらアミンまたは酸の
濃度は処理溶液の全量の０．０５〜５重量％好ましくは
０．１〜１重量％程度が適している。In addition, as the acid used, inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid, and organic acids such as formic acid, acetic acid, oxalic acid, and toluenesulfonic acid can be used. When an aqueous acid solution is used, the water in the aqueous solution hydrolyzes the halogenosilyl group or alkoxysilyl group of the fluorine-containing silane compound to form a hydroxysilyl group, increasing intermolecular condensation;
Or, if the wax component has a hydroxyl group, it has the effect of chemically reacting with that component. Furthermore, the acid and amine serve as catalysts that promote this hydrolysis and dehydration condensation. The concentration of these amines or acids is suitably about 0.05 to 5% by weight, preferably about 0.1 to 1% by weight, based on the total amount of the treatment solution.
本発明のワックス添加剤はそのペルフルオロアルキル基
によって優れた撥水、撥油性、非粘着性、防汚性をワッ
クスに付与する。更に、該ワックス添加剤上記ペルフル
オロ基と親無機物質基を有するので、有機溶剤のワック
ス除去作用に対しても優れた抵抗性を発揮する。The wax additive of the present invention imparts excellent water repellency, oil repellency, non-stick property, and stain resistance to wax through its perfluoroalkyl group. Furthermore, since the wax additive has the above-mentioned perfluoro group and an inorganic parent group, it exhibits excellent resistance to the wax removal action of organic solvents.
以下、実施例により本発明を具体的に説明する。 Hereinafter, the present invention will be specifically explained with reference to Examples.
実施例１
市販天然ワックス（ホホバ油：香栄興業（株）＋１２）
１００ｇを加温溶融し、これに含フツ素シラン化合物
Ｃ３Ｆ０７ Ｃ８２Ｃ）＋２３ｉ （ＯＣＨ３）３を５
ｇ添加し、５分間攪拌した後、スライドガラスに塗布し
た。この表面の水に対する接触角を測定したところ１１
８＠であった。Example 1 Commercially available natural wax (jojoba oil: Koei Kogyo Co., Ltd. +12)
100 g of fluorine-containing silane compound C3F07C82C)+23i (OCH3)3 was added to this by heating and melting.
After stirring for 5 minutes, it was applied to a slide glass. When the contact angle of this surface with water was measured, it was 11
It was 8@.
比較例１
実施例１と同一のワックスについて含フツ素シラン化合
物を添加せずに実施例１と同様の処理を行った。水に対
する接触角は７６°であった。Comparative Example 1 The same wax as in Example 1 was subjected to the same treatment as in Example 1 without adding the fluorine-containing silane compound. The contact angle with water was 76°.
実施例２
加温溶融した市販石油ワックス（エッソ石油（株）製：
商品名ニスパックス） １００ｇに、含フツ素シラン化
合物
しｉｚ １．＋ｒ１２ Ｌ＋１３
３．５ｇを添加し１０分攪拌した後に石油エーテルの１
０％希釈溶液とし、これを市販西洋紙に５分間含浸させ
た。Example 2 Commercial petroleum wax melted by heating (manufactured by Esso Oil Co., Ltd.:
(Product name: Nispax) 1. Add a fluorine-containing silane compound to 100 g. After adding 3.5 g of +r12 L+13 and stirring for 10 minutes, add 1 of petroleum ether.
A 0% diluted solution was prepared, and commercially available Western paper was impregnated with this for 5 minutes.
この上に、水滴、およびエチレングリコールを滴下し、
それが完全に吸収されるまでの時間を測定した。吸収時
間は水で３時間以上、エチレングリコールで１時間２０
分以上を要した。On top of this, drop water and ethylene glycol,
The time until it was completely absorbed was measured. Absorption time is 3 hours or more for water and 1 hour for ethylene glycol.
It took more than a minute.
比較例２
実施例２と同一のワックスについて、含フツ素シラン化
合物を添加せずに実施例２と同様の処理を行った。吸収
時間は水で２時間以上、エチレングリコールで１５分で
あった。Comparative Example 2 The same wax as in Example 2 was subjected to the same treatment as in Example 2 without adding the fluorine-containing silane compound. The absorption time was over 2 hours for water and 15 minutes for ethylene glycol.
実施例３
市販合成ワックス（ヘキストジャパン（株）製：商品名
へキストワックスＳ）１００ｇに、含フッ素シラン化合
物Ｃ，Ｆ工、 Ｃ０ＮＨ（ＣＩｌ□）ａ Ｓｉ （ＯＣ
ａ Ｈ５）３３．５ｇとトルエン３．５ｇの混合液を添
加し加温して１０分間攪拌した後、スライドガラスに塗
布した。Example 3 Fluorine-containing silane compounds C, F, C0NH (CIl
A mixed solution of 33.5 g of H5) and 3.5 g of toluene was added, heated and stirred for 10 minutes, and then applied to a slide glass.
この表面の水および流動パラフィンに対する接触角を測
定した。表面接触角は水で１１３°、流動パラフィンで
７２″であった。The contact angle of this surface to water and liquid paraffin was measured. The surface contact angle was 113° with water and 72″ with liquid paraffin.
比較例３
実施例３と同一のワックスについて、含フツ素シラン化
合物を用いずに、実施例３と同様の処理を行なった。表
面接触角は水で９１°、流動パラフィンで２８’であっ
た。Comparative Example 3 The same wax as in Example 3 was subjected to the same treatment as in Example 3 without using the fluorine-containing silane compound. The surface contact angle was 91° with water and 28' with liquid paraffin.
比較例４
本発明に係る含フツ素シラン化合物の代わりに、既知の
含フツ素界面活性剤Ｃ７Ｆ、 ５ＣＯ２Ｈ（新秋田化成
（株）製：商品名ＥＦＴＯＰ−２０１）を用いた以外は
実施例３と同様の処理を行った。表面接触角は水で８４
°、流動パラフィン３０″′であった。Comparative Example 4 Example 3 except that known fluorine-containing surfactants C7F and 5CO2H (manufactured by Shin-Akita Kasei Co., Ltd.: trade name EFTOP-201) were used instead of the fluorine-containing silane compound according to the present invention. The same process was performed. The surface contact angle is 84 with water.
°, liquid paraffin 30'''.
Claims (1)
＿３＿−＿ｌＸ＿ｌ（ I ）（式中Ｒ＿ｆは炭素数４〜
１２のペルフルオロアルキル基、ｎは０〜３の整数、ｍ
、ｌは１〜３の整数、ＹはＣＨ＿２、ＣＨ＿２Ｏ、ＮＲ
＾１、ＣＯ＿２、ＣＯＮＲ＾１、Ｓ、ＳＯ＿２、ＳＯ＿
２ＮＲ＾１、Ｒ＾１は水素、または炭素数１〜５のアル
キル基、Ｒ＾２は炭素数１〜５のアルキル基、ＸはＣｌ
、Ｂｒ、または炭素数１〜５のアルコキシ基）で表され
る含フッ素シラン化合物からなるワックス添加剤。 ２、含フッ素シラン化合物が一般式 Ｃ＿８Ｆ＿１＿７ＳＯ＿２ＮＲ＾２ＣＨ＿２ＣＨ＿２Ｃ
Ｈ＿２ＳｉＲ＾２＿３＿−＿ｌＸ＿ｌ（II）（式中Ｒ＾
２、Ｘは前記に同じ） であることを特徴とする請求項１のワックス添加剤。[Claims] 1. General formula R_f(CH_2)_nY(CH_2)_mSiR^2
_3_−_lX_l(I) (in the formula, R_f has 4 to 4 carbon atoms
12 perfluoroalkyl groups, n is an integer of 0 to 3, m
, l is an integer from 1 to 3, Y is CH_2, CH_2O, NR
^1, CO_2, CONR^1, S, SO_2, SO_
2NR^1, R^1 is hydrogen or an alkyl group having 1 to 5 carbon atoms, R^2 is an alkyl group having 1 to 5 carbon atoms, and X is Cl
, Br, or an alkoxy group having 1 to 5 carbon atoms). 2. The fluorine-containing silane compound has the general formula C_8F_1_7SO_2NR^2CH_2CH_2C
H_2SiR^2_3_-_lX_l(II) (in the formula R^
2. The wax additive according to claim 1, wherein X is the same as defined above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23698089A JP2629975B2 (en) | 1989-09-14 | 1989-09-14 | Water and oil repellent wax additives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23698089A JP2629975B2 (en) | 1989-09-14 | 1989-09-14 | Water and oil repellent wax additives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03100060A true JPH03100060A (en) | 1991-04-25 |
| JP2629975B2 JP2629975B2 (en) | 1997-07-16 |
Family
ID=17008610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23698089A Expired - Lifetime JP2629975B2 (en) | 1989-09-14 | 1989-09-14 | Water and oil repellent wax additives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2629975B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5435839A (en) * | 1992-12-24 | 1995-07-25 | Matsushita Electric Industrial Co., Ltd. | Finishing agents and method of manufacturing the same |
| US5545255A (en) * | 1992-05-27 | 1996-08-13 | Matsushita Electric Industrial Co., Ltd. | Finishing agent and method of using the same |
| US5849369A (en) * | 1995-06-14 | 1998-12-15 | Matsushita Electric Industrial Co., Ltd. | Method for manufacturing a chemically adsorbed film and a chemical adsorbent solution for the method |
| US6063438A (en) * | 1995-06-14 | 2000-05-16 | Matsushita Electric Industrial Co., Ltd. | Finishing agents and method of using the same |
| KR101986168B1 (en) * | 2018-02-20 | 2019-06-05 | 한국생산기술연구원 | Coating liquid applicable to radiation fins for LED with dust collection prevention and self-cleaning function and manufacturing method thereof |
-
1989
- 1989-09-14 JP JP23698089A patent/JP2629975B2/en not_active Expired - Lifetime
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5545255A (en) * | 1992-05-27 | 1996-08-13 | Matsushita Electric Industrial Co., Ltd. | Finishing agent and method of using the same |
| US5876806A (en) * | 1992-05-27 | 1999-03-02 | Matsushita Electric Industrial Co., Ltd. | Finishing agent and method of using the same |
| US5435839A (en) * | 1992-12-24 | 1995-07-25 | Matsushita Electric Industrial Co., Ltd. | Finishing agents and method of manufacturing the same |
| US5645633A (en) * | 1992-12-24 | 1997-07-08 | Matsushita Electric Industrial Co., Ltd. | Finishing agents and method of manufacturing the same |
| US5849369A (en) * | 1995-06-14 | 1998-12-15 | Matsushita Electric Industrial Co., Ltd. | Method for manufacturing a chemically adsorbed film and a chemical adsorbent solution for the method |
| US5907013A (en) * | 1995-06-14 | 1999-05-25 | Matsushita Electric Industrial Co., Ltd. | Method for manufacturing a chemically adsorbed film and a chemical adsorbent solution for the method |
| US6060123A (en) * | 1995-06-14 | 2000-05-09 | Matsushita Electric Industrial Co., Ltd. | Method for manufacturing a chemically adsorbed film and a chemical adsorbent solution for the method |
| US6063438A (en) * | 1995-06-14 | 2000-05-16 | Matsushita Electric Industrial Co., Ltd. | Finishing agents and method of using the same |
| US6287633B1 (en) | 1995-06-14 | 2001-09-11 | Matsushita Electric Industrial Co., Ltd. | Finishing agents and method of using the same |
| US6548116B2 (en) | 1995-06-14 | 2003-04-15 | Matsushita Electric Industrial Co., Ltd. | Method for manufacturing a chemically adsorbed film and a chemical adsorbent solution for the method |
| KR101986168B1 (en) * | 2018-02-20 | 2019-06-05 | 한국생산기술연구원 | Coating liquid applicable to radiation fins for LED with dust collection prevention and self-cleaning function and manufacturing method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2629975B2 (en) | 1997-07-16 |
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